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One passenger / one way
- This trip is recommended because it is: Cheapest + FastestDeparture time: May 2 atDeparture city: WinonaDeparture location: Winona StationArrival time: May 2 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: Amtrak
Vehicle: TrainDuration: - Departure time: May 2 atDeparture city: WinonaDeparture location: Winona StationArrival time: May 2 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: May 2 atDeparture city: WinonaDeparture location: Winona StationArrival time: May 2 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: May 2 atDeparture city: WinonaDeparture location: Winona StationArrival time: May 2 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: May 2 atDeparture city: WinonaDeparture location: Winona StationArrival time: May 2 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
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Compare 2 ways to go from Winona to Chicago.
Busbud recommends taking the train from Winona to ChicagoAmong the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 5 hours 44 minutes and with fares starting at just $39, it presents an excellent value for a comfortable ride.
Train Winona to Chicago: Trip Overview
Please note, this information is subject to change.
Train Companies
Based on 5090 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $39.00
Winona to Chicago Train
With Busbud, comparing and booking tickets for a train from Winona to Chicago is a breeze. Browse through an extensive selection of train fares and train schedules to find the best deals.
We make it our job to connect you with the most dependable companies that offer train service from Winona to Chicago.
From train tickets to high-end trains trip from Winona to Chicago, we offer a wide range of train services to best suit your needs depending on how much your budget is.
Frequently asked questions for your trip Winona - Chicago
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Winona to Chicago was searched and found on Apr 30, 2025 with a price of $36To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Winona to Chicago, as early as possible.
You can expect to pay from $36 to $487 for a train ticket from Winona to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $36 which is on 2025-05-03.
About Train Travel
Train Travel Tips
Taking the fastest trains allows you to travel at speeds greater than 300 km/h. Taking a trip from Winona to Chicago is not only much quicker but more comfortable too! You can usually travel directly to the city centre and save time while you're at it.
Whether you take a regional or high-speed train to Chicago, you’ll help reduce the environmental impact and carbon footprint of your trip. As you watch the landscapes unfold before your eyes, you can tell yourself that with this choice, you are making sure they remain protected.
The train emits up to 30x less CO2 for a trip between Winona and Chicago compared to the same trip made by plane or car. A truly ecological mode of transport that will allow you to easily reduce your carbon footprint.
Tune out to the fine sounds of your best music playlist on your train trip from Winona to Chicago while indulging in miles on end of beautiful scenic views.
Did you know?
New York holds the record for the most platforms and track numbers in a single station. Grand Central Station in Manhattan is one of the largest rail terminals in the world with more than 44 platforms and 67 tracks to accommodate passengers.
Railway companies played a major role as early as 1883 in the use of time zones as we know them today.
Japanese trains are always on time, it is extremely infrequent to see breakdowns during peak periods. In the event of a delay of more than 5 minutes, the crew will personally apologize to each passenger.
Top Traveled Train Routes
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